Perilla seed composition

ABSTRACT

A composition of matter comprises a shelf stable, partially defatted supercritical CO 2  fluid solvent extracted whole grain flour derived from a cracked biomass of  perilla frutescens , the flour comprising minerals and 2 to 8 percent of native seed oil, 35 to 45 percent protein, and 35 to 45 percent fiber.

RELATED APPLICATION(S)

This is a continuation-in-part application of application Ser. No. 13/231,131 filed Sep. 13, 2011, which is a continuation-in-part application of application Ser. No. 12/419,321 filed Apr. 7, 2009, which is based upon provisional application Ser. No. 61/043,773 filed Apr. 10, 2008, the disclosures which are hereby incorporated by reference in their entirety.

FIELD OF THE INVENTION

This invention relates to plant-derived perilla seed products.

BACKGROUND OF THE INVENTION

The copending and commonly assigned U.S. patent application Ser. No. 13/231,131 discloses a composition of matter that comprises a shelf stable, super critical, CO² fluid extracted seed oil derived from a cracked biomass of perilla frutescens, the seed oil comprising from about 60 to about 95 percent w/w of PUFAs in a ratio of from about 4:1 to about 6:1 alpha-linolenic acid (ALA) to linoleic acid (LA) and a mixture of selected antioxidants.

A process for forming the perilla seed extract is also disclosed by subjecting the pre-milled cracked or flake-rolled seed to supercritical CO² extraction. A partially or wholly defatted perilla seed as a cake residue with virtually no fat or oil is disclosed as one of the by-products. The extracted oil in one example is the desired end product. The defatted cake resulting from the supercritical CO2 process is disclosed as potentially viable. It is desirable to process the partially defatted cake to use as a dietary supplement, food or beverage.

SUMMARY OF THE INVENTION

A composition of matter comprises a shelf stable, partially defatted supercritical CO² fluid solvent extracted whole grain flour derived from a cracked biomass of perilla frutescens, the flour comprising minerals and 2 to 8 percent of native seed oil, about 35 to 45 percent protein and 35 to 45 percent fiber.

In one example, the native seed oil comprises 1 to 4 percent ALA and about 0.2 to 0.8 percent LA. In another example, the fiber comprises about 32 to 40 percent insoluble fiber and about 2 to 6 percent soluble fiber. The composition may exhibit pH dependent thixotropic properties when mixed with water. The flour may further comprise lipophilic additives comprising at least one of rosemary oil, tocopherols, tocotrienols, carotenoids, seed oils, lipophilic solvent extracted botanical oils, lipophilic food flavorings, polyunsaturated fatty acid esters. In another example, the flour may further comprise hydrophilic additives comprising at least one of hydrophilic solvent extracts of botanicals, green tea extract, grape seed extract, ascorbic acid, caffeine, mono and/or polysaccharides, gums, phospholipids, biopolymers, or hydrophilic food flavorings. The flour may comprise about 2 to 3 percent of fructo-oligosaccharides in yet another example. A delivery product may comprise a beverage, protein shake, nutritional bar, confectionary filling, icing, pasta, processed meat, peanut butter or jelly.

In another example, the composition of matter comprises a shelf stable, partially defatted, perilla frutescens derived, whole grain flour comprising minerals and about 2 to B percent of native seed oil, about 35 to 45 percent protein and about 35 to 45 percent fiber. The perilla frutescens derived, whole grain flour in one example is made by pre-milling or roller press flaking perilla frutescens seed in the absence of oxygen to obtain a cracked seed biomass and subjecting the cracked seed biomass to supercritical fluid CO2 extraction to produce the flour with or without lipophilic and/or hydrophilic antioxidants.

A method is also disclosed of treating gastrointestinal irregularities and/or cardiovascular disease in humans or animals by administering an effective amount of a dietary supplement, food or beverage that has added thereto the composition mixed therewith and comprising a shelf stable, partially defatted supercritical CO2 fluid solvent extracted whole grain flour derived from a cracked biomass of perilla frutescens, the flour comprising minerals and about 2 to 8 percent of native seed oil, about 35 to 45 percent protein and about 35 to 45 percent fiber.

The method further comprises forming a beverage, liquid concentrate, or dried beverage pre-mix to which the composition is added. The method further comprises preparing liquid concentrates or dried pre-mixes including protein shakes, fruit smoothies, ready-to-drink beverages, dry beverage pre-mixes, frozen fruit concentrates, aqueous alcoholic beverage pre-mixes, concentrates or their dried pre-mixes, vitamin, carbohydrate and protein fortified meal replacement beverages, drinkable dairy and non-dairy yogurts, gravies and dry gravy pre-mixes, and ready-to-drink and dried pre-mixed infant formulas. The method further comprises thickening the resulting final beverage by adding one or more acidulants for adjusting the pH from between about 3 to about 6.5.

BRIEF DESCRIPTION OF THE DRAWINGS

Other objects, features and advantages of the present invention will become apparent from the detailed description of the invention which follows, when considered in light of the accompanying drawings in which:

FIG. 1 is a flowchart illustrating a production diagram as a flowchart for producing omega-3 chia seed oil such as sold under the tradename Chia Gold™ by Valensa International of Eustis, Fla.

FIG. 2 is another production diagram as a flowchart showing basic steps for manufacturing a perilla seed extract in accordance with a non-limiting example.

FIG. 3 is another production diagram as a flowchart showing basic steps for manufacturing the perilla seed flour in accordance with a non-limiting example.

DETAILED DESCRIPTION OF THE EMBODIMENTS

The present invention will now be described more fully hereinafter. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the invention to those skilled in the art.

It is well known in the literature that Polyunsaturated Fatty Acids (PUFAs) of all types are highly susceptible to peroxide, free radical and light induced degradation including rancification and polymerization making them unsuitable for human consumption. For example, it is well known that flax seed oil, also known as linseed oil, readily undergoes free radical oxidation to advantageously form polymeric surfaces including oil based paints, hard furniture finishes and linoleum flooring. In addition, many companies offer flax seed oil for human consumption as a dietary supplement or food ingredient because of the high levels of PUFAs found in raw flax seed and its expeller pressed oils and more particularly Alpha-Linolenic Acid (ALA) and Linolenic Acid (LA). Many flax seed oil product labels suggest that the product must be refrigerated at all times due to the instability of such PUFAs in flax seed oil. Careful examination of the majority of commercially available flax seed oils obtained by expeller pressing, including those typically stored under refrigerated conditions, unfortunately reveals that they are unfit for human use based on their measured Peroxide Values (PVs). Such PV values above 3 meg/Kg (milliequivalents/gram) are deemed not suitable for salad oil applications and PV values above 10 meq/Kg are deemed to be unsuitable for human use because the measured PV value may be an early indicator of rancidity and free radical induced degradation. On the other hand, PV values taken alone do not adequately characterize such oils since a low PV value can also be associated with PUFA's that have already gone through the rancification process. Typical testing has revealed flax seed oil products sold for human consumption with observed PV's as high as 130 meq/kg also characterized with the odor associated with short chain aldehydes that make such oils “rancid” to olefactory senses.

Most raw seed based oils in common cooking and baking use, such as soybean, corn and canola seed oils naturally contain enough PUFAs making them unsuitable, without further processing, for use as cooking oils. Therefore unless such PUFA containing raw seed oils are hydrogenated to fully saturated triglycerides using hydrogen and a catalyst prior to their use in cooking applications, they are considered to be unfit for use as cooking oils. These oils are typically first isolated by, for example, expeller pressing the appropriate seed. The crude seed oil is then filtered to remove biomass. The resulting oil, containing significant levels of PUFAs, is then catalytically hydrogenated to reduce the PUFA content to levels suitable for use of the resulting oil in cooking applications. If the hydrogenation process is incomplete, however, the resulting mixtures are found to contain both undesirable heat labile PUFAs that quickly undergo rancification to small chain aldehydes in the resulting heated cooking oil as well as unsaturated trans-fatty acids which are believed to be detrimental to animal and especially human health.

Therefore, those skilled in the art will recognize the great difficulty in producing a shelf stable PUFA mixture wherein the PUFA content is as high as 70% wt/wt of the resulting seed extract from a natural seed source that then exhibits extraordinary room temperature stability.

Commonly assigned and copending patent application Ser. No. 12/419,321 discloses a Salvia hispanica L. derived seed oil extract composition of matter containing from 60-88% PUFAs in a ratio of from 3.1:1-3.3:1 of ALA to LA, 4-10% of C-18 mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8% of C-16 saturated fatty acid in a mixed triglyceride form stable at room temperature of 12-24 months containing a mixture of selected antioxidants. This chia derived composition has a very favorable ratio of ALA to LA (omega 3 to omega 6) of about 3.3:1 in one example.

Commonly assigned and copending U.S. patent application Ser. No. 13/231,131 discloses a perilla seed oil extract that provides a healthy source of omega-3 and contains a very favourable ratio of ALA to LA (omega-3 to omega-6) of about 6:1 in one example. The perilla oil is obtained by pressing the perilla seeds to initiate seed cracking, processing the cracked biomass using supercritical CO² fluid extraction, and collecting the extract to deliver more of the higher molecular weight compounds.

This perilla seed derived flour is formed as a shelf stable, supercritical, CO² fluid extracted seed oil derived from a cracked biomass of perilla frutescens, the seed oil comprising from about 60 to about 95 percent w/w of PUFAs in a ratio of from about 4:1 to about 6:1 alpha-linolenic acid (ALA) to linoleic acid (LA) and a mixture of selected antioxidants.

In one example the selected antioxidants are formed as a synergistic mixture of selected lipophilic and hydrophilic antioxidants. In another example the composition includes lipophilic antioxidants either alone or in combination with at least one of: a) phenolic antioxidants including at least one of sage, oregano, and rosemary; b) tocopherol, c) tocotrienol(s), d) carotenoids including at least one of astaxanthin, lutein, and zeaxanthin; e) ascorbylacetate; f) ascorbylpalmitate g) Butylated hydroxytoluene (BHT); h) Docosapentaenoic Acid (BHA) and i) Tertiary Butyl hydroquinone (TBHQ). In another example a hydrophilic antioxidant or sequesterant is added comprising hydrophilic phenolic antioxidants including at least one of grape seed extract, tea extracts, ascorbic acid, citric acid, tartaric acid, and malic acid.

In an example the peroxide value of the seed oil is under 10.0 meg/Km. The composition may be supplemented with docosahexaenoic acid (DHA) and/or eicosapentaenoic acid (EPA) in pectin or gelatin based confectionary dietary supplement delivery systems. The composition may include EPA, DHA, docosapentaenoic acid (DPA) or gamma-linlolenic acid (GLA), fish oil, krill oil, krill oil concentrate, borage oil, evening primrose oil, olive oil or other plant, animal or algal based seed or fruit oils admixed therein. This seed oil may be shelf stable at room temperature up to 32 months.

A method is also disclosed of mitigating or preventing cardiovascular disease, arthritic pain and inflammation, platelet aggregation, or treating dry eye syndrome, premenstrual symptoms or modifying immune response in humans or animals by applying an effective amount of a dietary supplement, food or beverage that has added thereto a composition mixed therewith and comprising a supercritical, CO² fluid extracted seed oil derived from a cracked biomass of perilla frutescens, the seed oil comprising from about 60 to about 95 percent w/w of PUFAs in a ratio of from about 4:1 to about 6:1 alpha-linolenic acid (ALA) to linoleic acid (LA) and a mixture of selected antioxidants.

A method of manufacturing a perilla frutescens derived seed oil was disclosed with the seed oil comprising from about 60 to about 95 percent w/w of PUFAs in a ratio of from about 4:1 to about 6:1 alpha-linolenic acid (ALA) to linoleic acid (LA). The method included processing perilla frutescens seed preferably in the absence of oxygen to obtain a biomass having a desired particle size distribution, subjecting the resulting biomass to supercritical fluid CO² extraction, collecting a resulting seed oil fraction, and separating water in the fraction.

The commonly assigned and copending patent application Ser. No. 12/419,321 discloses the oil extract as a room temperature, shelf stable mixture of an approximate 3.1:1 to about 3.3:1 mixture of alpha-linolenic acid (“ALA”, “Omega-3 polyunsaturated fatty acid” (“PUFA”)) to linoleic acid (“LA”, “Omega-6 PUFA) that has been prepared in the presence of limited amounts of saturated and mono-unsaturated fatty acids as their mixed triglycerides by the use of either supercritical fluid CO² solvent extraction of pre-milled Salvia hispanica L. seed alone, and more particularly, supercritical fluid CO² solvent extraction in the presence of mixtures of hydrophilic and lipophilic antioxidants, or, by the use of a common organic solvent extraction such as hexane or by the use of expeller pressing techniques. The supercritical CO² extraction is preferred.

Such Omega-3 and Omega-6 PUFAs are well known as essential fatty acids in man and many animals, which are useful in humans and animals in promoting, for example, a heart healthy condition in man. It is also well known, however, that PUFAs are extremely susceptible to rapid, uncontrollable free radical mediated degradation.

The composition of matter disclosed in the copending '321 application includes a supercritical CO² Salvia hispanica L. derived seed oil comprising from 60-88% PUFAs in a ratio of from about 3.1:1-3.3:1 of alpha-linolenic acid (ALA) to linoleic acid (LA), 4-10% of C-18 mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8% of C-16 saturated fatty acid in a mixed triglyceride form that is stable at room temperature for 12-24 months and comprising a mixture of selected antioxidants.

That composition of matter disclosed in the '321 application includes dietary supplement ingredients such as docosahexaenoic acid (DHA) and/or eicosapentaenoic acid (EPA) in pectin or gelatin based confectionary dietary supplement delivery systems. EPA, DHA, docosahexaenoic acid (DPA) or gamma-linlolenic acid (GLA), fish oil, krill oil, krill oil concentrate, borage oil, evening primrose oil, olive oil or other plant, animal or algal based seed or fruit oils are admixed therein either alone or in combination. Lipophilic antioxidants are added either alone or in combination with at least one of a) phenolic antioxidants including at least one of sage, oregano, and rosemary; b) tocopherol, c) tocotrienol(s), d) carotenoids including at least one of astaxanthin, lutein, and zeaxanthin; e) ascorbylacetate; f) ascorbylpalmitate g) Butylated hydroxytoluene (BHT); h) Docosapentaenoic Acid (BHA) and i) Tertiary Butyl hydroquinone (TBHQ). As disclosed, a hydrophilic antioxidant or sequesterant includes hydrophilic phenolic antioxidants including at least one of grape seed extract, tea extracts, ascorbic acid, citric acid, tartaric acid, and malic acid.

A method of manufacturing and method of using the composition is also set forth in the '321 application.

As further disclosed in the incorporated by reference '321 application, this PUFA rich seed oil extract is prepared from Salvia hispanica L. seed which contains one of nature's more favorable seed based concentrations and ratios for the essential fatty acids, and more specifically, the essential fatty acids ALA and LA in a ratio of approximately 3.3:1 as a mixture of ALA and LA that is stable at room temperature for long periods of time when desirably and appropriately treated with antioxidants either before, during, or after (or any combination thereof). A shelf life of 12-24 months has been found.

Such oils are used either alone or advantageously in combination with other ingredients, for example, algae, plant or fish derived alpha-linolenic acid (ALA) or linoleic acid (LA) metabolites such as eicosapentaenoic acid (EPA), docosapentaenoic acid (DPA), gamma-linlolenic acid (GLA) or docosahexaenoic acid (DHA) or any combination thereof, incorporated into appropriate foods, beverages or dietary supplements for the prevention or mitigation of such diseases as cardiovascular disease, arthritis, pain, blood clotting, dry eyes and brain health.

Such disease mitigation has been associated with the competitive control of the LA metabolic cascade and the resulting metabolic cascade products from LA metabolism known commonly as eicosanoids, such as the series 2 and 3 prostaglandins and thromboxanes, the series 4 leucotrienes and lipoxins and the series 5 leuotrienes all of which are potent platelet aggregators and/or inhibitors, pro-inflammatories, vasodilators, bronchoconstrictors, or anti-asthmatics and the like.

The consumption of ALA has been shown to be a very effective competitive substrate of delta-6 desaturase, which is known to be the rate limiting enzymatic step in both ALA and LA metabolism to the metabolic products discussed above.

Attempted extraction of Saliva hispanica L. unmilled seed, using supercritical CO² even at extraordinarily high pressures of 1000 bar or hexane solvent at atmospheric pressures, yields very little, if any, seed oil, therefore the seed is milled prior to extraction. The extent of the milling, as measured by particle size distribution, is advantageous to the extraction process in accordance with a non-limiting example since the higher the surface area, the higher will be the efficiency and completeness of the extraction process by either organic solvent based or supercritical fluid based processes. In addition, it is often advantageous to mill the seed in a blanket of inert gas such as nitrogen to prevent per-oxidative processes from taking place that would otherwise be initiated in the presence of air or oxygen and light.

In one embodiment, whole seed is either first commutated in a standard knife or hammer mill or more preferably roller milled, preferably under a cold nitrogen atmosphere, to produce a cracked seed biomass. The seed biomass is preferably treated with one or more hydrophilic and/or lipophilic antioxidants by mixing the antioxidants to the resulting biomass. In another embodiment, the antioxidant may be advantageously added to the seed prior to or during the milling process or at the point of extraction without pre-blending the antioxidants evenly throughout the resulting biomass due to the nature of the extraction process. The biomass is then transferred to a supercritical fluid extraction unit for separation of the seed oil from the cracked or flake-rolled biomass.

Alternatively, the pre-prepared biomass can be transferred to a common hexane solvent extractor, or an expeller press for example, and the oil extracted from the biomass accordingly. Preferably either process is conducted in the absence of oxygen or air.

The supercritical fluid extraction of the milled seed admixed with hydrophilic and/or lipophilic antioxidants is accomplished by subjecting the pre-milled cracked or flake-rolled seed to supercritical CO², or CO² and propane as a co-solvent, or supercritical propane alone at from 40-1000 bar at from 30-100 Deg. C. More preferably the seed oil is extracted from the biomass between 50-800 bar at 50-90 deg. C. in such CO² amounts measured in kgs/kg of biomass and for such times as may be required to extract large portions of the seed oil content from the biomass. In addition, entrainment solvents can be added to the supercritical fluid to further enhance the efficacy of such extractions. For example, supercritical carbon dioxide extraction of the biomass can be enhanced by the addition of propane to the supercritical extraction fluid.

The resulting seed oil dissolved in supercritical solvent(s) is next allowed to fractionate in two separate pressure step-down stages allowing the collection of a light and heavy fraction of seed oil extract. This light fraction also contains water that has been co-extracted from the seed mass. The resulting seed oil, after degassing, is separated from any water that may have been carried over during the extraction of the biomass containing the water. The light fraction of the seed oil extract is rich in taste and odor components and may be admixed with the heavy fraction or may be discarded depending on the desired product characteristics.

After separation of the water remaining in each fraction, the fractions are then held under nitrogen or other inert gas and additional amounts of lipophilic and/or hydrophilic antioxidants may then be added. In addition, the resulting fractions may also be treated with bleaching clay, carbon and such other processing aids as may be required to render the oil suitable for its intended use in humans and animals.

The PV of the resulting seed oil extract is typically under 2.0 meq/Km, while accelerated decomposition, using a Rancimat instrument, remarkably indicates an extrapolated room temperature shelf life of from about 1-2 years. When the same process is repeated without the use of antioxidants, the resulting PV is surprisingly under 10.0 meq/Kg most probably due to the use of supercritical CO² resulting in minimal exposure of the oil to oxygen species. However, the resulting oil quickly begins to build peroxide value in the presence of air even when stored at temperatures of 0 begs. C. In addition, such unstabilized oils, under accelerated rancimat testing exhibit very poor stability to heat and oxygen unlike the rancimat performance observed in stabilized oils derived from the process described above.

The resulting supercritical fluid seed oil extract contains from 60-88% PUFAs in a ratio of from 3.1:1-3.3:1 of ALA:LA, 4-10% of C18 mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8% C-16 saturated fatty acid composition in a mixed triglyceride form depending on the seed source employed.

On the other hand, if the process described above is conducted without the use of hydrophilic and/or lipophilic antioxidants, the resulting seed oil extract exhibits an initial low PV but accelerated stability testing using a Rancimat instrument indicates an extrapolated room temperature shelf stability of less than two months.

The stability of the resulting oil at room temperature that is manufactured without the use of added antioxidants is easily explained because of the available levels of the powerful natural antioxidants found in Salvia hispanica L. whole seed whose activity can be easily measured in Oxygen Radical Absorbance Capacity (ORAC) units. Salvia hispanica L. has a measured ORAC number of 3000 micromoles TE ORAC units/gram of seed and is known to contain such antioxidants as myricetin, quercetin, kaempferol, caffeic acid, and chlorogenic acid. In addition, it is well known that the example Salvia hispanica L. whole seed, unlike many other seeds bearing PUFA containing oil, exhibits a shelf life of at least 5 years due to its structure and the naturally occurring antioxidants available in the seed matrix.

In addition, cold pressing of Salvia hispanica L. whole seed also produces unstable seed oil without careful addition of appropriate antioxidants to the seed prior to the expeller pressing process.

In a non-limiting example the composition of matter is formed from a supercritical CO² derived Salvia hispanica L. derived seed oil comprising from 60-88% PUFAs in a ratio of from 3.1:1-3.3:1 of alpha-linolenic acid (ALA) to linoleic acid (LA), 4-10% of C-18 mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8% of C-16 saturated fatty acid in a mixed triglyceride form that is stable at room temperature for 12-24 months and comprising a mixture of selected antioxidants.

It includes docosahexaenoic acid (DHA) and/or eicosapentaenoic acid (EPA) in pectin or gelatin based confectionary dietary supplement delivery systems and in another aspect EPA, DHA, docosapentaenoic acid (DPA) or gamma-linlolenic acid (GLA), fish oil, krill oil, krill oil concentrate, borage oil, evening primrose oil, olive oil or other plant, animal or algal based seed or fruit oils are admixed therein.

Lipophilic antioxidants are added either alone or in combination with at least one of a) phenolic antioxidants including at least one of sage, oregano, and rosemary; b) tocopherol, c) tocotrienol(s), d) carotenoids including at least one of astaxanthin, lutein, and zeaxanthin; e) ascorbylacetate; f) ascorbylpalmitate g) Butylated hydroxytoluene (BHT); h) Docosapentaenoic Acid (BHA) and i) Tertiary Butyl hydroquinone (TBHQ). The hydrophilic antioxidant or sequesterant includes hydrophilic phenolic antioxidants including at least one of grape seed extract, tea extracts, ascorbic acid, citric acid, tartaric acid, and malic acid in another aspect.

A method of manufacturing a Salvia hispanica L. derived seed oil in another non-limiting example is set forth. The seed oil comprises from 60-88% PUFAs in a ratio of from 3.1:1-3.3:1 of alpha-linolenic acid (ALA) to linoleic acid (LA), 4-10% of C-18 mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8% of C-16 saturated fatty acid in a mixed triglyceride form that is stable at room temperature for 12-24 months and includes antioxidants. The method includes milling or roller press flaking Salvia hispanica L. seed in the absence of oxygen to obtain a desired particle size distribution with or without the addition of hydrophilic or lipophilic antioxidants during the particle sizing process. The resulting biomass is subjected to supercritical fluid CO² extraction in the presence of lipophilic and/or hydrophilic antioxidants. Any resulting seed oil fractions are collected. The water is separated in each fraction.

Any resulting seed oil fractions can be treated with additional antioxidants to afford a desired room temperature stability. The extent of oil extraction can be controlled by particle size distribution of the milled or flaked seed. Propane can be added in mixture with supercritical CO² in the supercritical state as an extraction solvent. In yet another aspect solvent can be extracted using hexane extraction at or near atmospheric pressures and the resulting boiling point of hexane in the absence of oxygen, separating the resulting water from the oil/hexane mixture and removing the hexane solvent by distillation at or below atmospheric pressure in the absence of oxygen.

Lipophilic antioxidants can be added to increase the room temperature stability of the resulting oil. The lipophilic antioxidants can be added either alone or in combination with at least one of a) phenolic antioxidants including at least one of sage, oregano, and rosemary; b) tocopherol, c) tocotrienol(s), d) carotenoids including at least one of astaxanthin, lutein, and zeaxanthin; e) ascorbylacetate; f) ascorbylpalmitate g) Butylated hydroxytoluene (BHT); h) Docosapentaenoic Acid (BHA) and i) Tertiary Butyl hydroquinone (TBHQ). The resulting dewatered seed oil can be treated with bleaching clay or activated carbon.

Pre-milled or roller press flaked seed can be treated with a lipophilic or hydrophilic antioxidant(s) prior to solvent extraction. The hydrophilic antioxidant or sequesterant can be formed from hydrophilic phenolic antioxidants including at least one of grape seed extract, tea extracts, ascorbic acid, citric acid, tartaric acid, and malic acid.

A method of mitigating or preventing cardiovascular disease, arthritic pain and inflammation, platelet aggregation, or treating dry eye syndrome, premenstrual symptoms or modifying immune response in humans or animals is set forth by applying an effective amount of the dietary supplement, food or beverage to which has been a composition mixed therewith and comprising a Salvia hispanica L. derived seed oil comprising from 60-88% PUFAs in a ratio of from 3.1:1-3.3:1 of alpha-linolenic acid (ALA) to linoleic acid (LA), 4-10% of C-18 mono-unsaturated fatty acid, 1-5% of C-18 saturated fatty acid and 4-8% of C-16 saturated fatty acid in a mixed triglyceride form that is stable at room temperature for 12-24 months and includes antioxidants.

In one aspect, an emulsifying agent is added. In another aspect, nano- and/or micro-particles of rice or sugarcane based polycosanol are dispersed for enhancing a heart healthy dietary supplement. A stabilized oil in a fruit juice concentrate, fruit puree or other water based flavoring is dispersed in the presence of maltodextrin, or other carbohydrates, and a suitable emulsifying or emulsion stabilization agent that is vacuum spray dried to form an amorphous or crystalline solid suitable for use as a flavoring ingredient carrying stabilized PUFAs in flavored dietary supplements, foods and beverages. In yet another aspect, oil based flavors and fragrances suitable for use as an ingredient in foods, beverages and cosmetics are added. ALA and LA are also added as essential fatty acids.

In accordance with a non-limiting example, it has also been found that the use of a perilla seed oil extract instead of the disclosed chia seed oil extract is advantageous and contains a very favorable ratio of ALA to LA (omega-3 to omega-6) of as high as about 6:1 in some examples as compared to chia seed oil that is typically about 3.3:1 ALA to LA. Perilla seed oil extract as obtained, in accordance with a no-limiting example, is thus an even healthier source of omega-3 than chia seed oil in various non-limiting examples. The manufacturing techniques as described above may equally be applied to the perilla seed oil extract production.

FIG. 1 is a flowchart showing a production diagram for a sequence of steps for producing omega-3 chia seed oil such as sold under the tradename Chia Gold™ by Valensa International of Eustis, Fla. The salvia hispanica seed is provided (block 100) and seed cracking occurs (block 102) to form a cracked biomass. Various techniques for seed cracking and forming the biomass can be used as described above. The supercritical CO² extraction (block 104) uses ultra high pressure carbon dioxide extraction technology and supplied CO² (block 106) such as the DEEP EXTRACT® manufacturing process developed by Valensa International of Eustis, Fla. The defatted seed as a flour, for example, (block 108) is produced. Separation of the different portions occurs such as by fractionating the seed oil extract (block 110) as described above. The extract is collected (block 112). Dewatering and decantation occurs (block 114) and antioxidants are added (block 116) such as the OTB® Per Oxidation blocker system from Valensa International. Quality control analysis occurs (block 118) and the final oil packaged (block 120).

FIG. 2 shows a second production diagram as a flowchart for producing the perilla seed oil extract in accordance with a non-limiting example. The process begins with a source of the perilla seed also known as perilla frutescens seed (block 130).

Similar to the process with the omega-3 chia seed oil, seed cracking occurs (block 132) to form a cracked seed biomass followed by the extraction (block 134) using the supercritical CO² extraction and supplying carbon dioxide (block 136) to produce the defatted seed (block 138) that is partially or wholly defatted perilla seed as a cake residue with virtually no fat or oil. The other portion is the oil and the CO² is reclaimed (block 140). Similar to the omega-3 chia seed oil, the extract is collected (block 142) and dewatering and decantation occurs (block 144). Antioxidants such as the OTB® components as described before are added (block 146) and the quality control analysis occurs (block 148) followed by packaging (block 150).

The perilla seed extract can have a range of values for its fatty acid profile. Total fatty acids, peroxide values and other component values are described in Table 1 below showing an analysis of perilla seed extract and various parameters, specifications and results as a non-limiting example. Results can vary of course for different samples.

TABLE 1 Ingredients: Perilla ( Perilla frutescens (L) Britton) Seed Oil, O2B ™ Botanical peroxidation blocker including refined nonGMO soybean mixed tocopherols and spice extract. Parameter Specification Result Description Clear yellow oil, pourable Conforms Odor at room temperature Mild Conforms Solubility Insoluble in water, miscible Conforms with oils Fatty Acid Profile [%] VQP-050 (GC) Palmitic Acid 6.3 Stearic Acid 1.9 Oleic Acid 22.3 Linoleic Acid 9.7 α-Linolenic Acid >56 59.8 Total Fatty Acids (% w/w) 85 . . . 95 88.6 Peroxide Value (meqO₂/kg) <10 VQP-049 2.3 Water Content (%)  <1.5 VQP-048 <0.2 Heavy Metals (ppm) <10 ICP-MS <1 Microbiological Data (cfu/g) Total Aerobic Microbial Count <10³ USP <61> <100 Combined Yeast & Mold <10² USP <61> <100 E. coli/Total Coliforms <10 AOAC 991.14 <10 (all values as is basis) All of the ingredients are GMO free. Therefore this product is in accordance with EU regulations 1830/2003 and 1820/2003. The Product has not been treated with gamma rays.

Table 2 show accelerated stability testing of the perilla seed extract with an OTB® per oxidation blocker and Table 3 shows the accelerated stability testing of a perilla seed extract sample produced by Valensa International of Eustis, Fla. as compared to chia seed extracts such as the Chia Gold™ which is produced by the process shown in FIG. 1 and the Tresalbio Chia Oil.

TABLE 2 Accelerated Stability Testing of Valensa Perilla Seed Extract with O2B

Rancidity Induction Time Shelf Life @20° C. (hr)¹ (yr)² Perilla Oil (without O2B) 7 0.5 Perilla Oil (with O2B) 42 2.8 ¹Rancimat induction time measured in hours with air bubbling through heated oil (90° C.) in the light. ²Rancimat data is a function of accelerated high heat and oxygen exposure. Extrapolated data plots are assumed linear in the presence of air and light at 20° C. however, if product is stored at 20° C. in an air and light barrier package, then shelf stability is at least doubled.

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TABLE 3 Accelerated Stability Testing of Valensa Perilla Seed and Chia Seed Extracts with O2B

Shelf Rancidity Shelf Life Induction Time Life @20° C. Increase (hr)¹ (yr)² (%) Perilla Oil (without O2B) 7 0.5 Perilla Oil (with O2B) 42 2.8 611% Tresalbio Chia Oil (without 12 0.4 O2B) Tresalbio Chia Oil (with O2B) 73 2.2 603% ChiaGold Oil (without O2B) 9 0.3 ChiaGold Oil (with O2B) 60 1.8 663% ¹Rancimat induction time measured in hours with air bubbling through heated oil (80-90° C.) in the light. ²Rancimat data is a function of accelerated high heat and oxygen exposure. Extrapolated data plots are assumed linear in the presence of air and light at 20° C. however, if product is stored at 20° C. in an air and light barrier package, then shelf stability is at least doubled.

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Table 1 illustrates various values and shows the total fatty acids (% w/w) is about 85 to about 95 and has in that particular example a result of 88.6. It should be understood that the seed oil could possibly have as low as about 60% w/w of PUFAs and as high as about 95% and a ratio of from about 4:1 to about 6:1 ALA to LA. The peroxide value of the seed oil is typically under 10.0 meq/Km. The PUFAs typically comprise at least greater than 50% ALA and in the example shown in Table 1 is greater than 56% and in one particular example shown in FIG. 1 is 59.8. The seed oil is shelf stable at room temperature up to 32 months in a particular example. Other data is shown such as specific components of the fatty acids and the water content, heavy metals in PPM, and microbiological data in CFU/G, such as the total aerobic microbial count, a combined yeast and mold and E. coli/total coliforms. All the values are an as-is basis and the ingredients are GMO free. Therefore, this product is in accordance with EU regulations 1830/2003 and 1829/2003. This product had not been treated with gamma rays. Ingredients include the perilla (perilla frutescens (L) Britton) seed oil, OTB® botanical per oxidation blocker including refined non-GMO soybean mixed tocopherols and spice extracts. GMO corresponds to genetically modified organisms, and thus, non-GMO refers to non-genetically modified organisms. The soybean had not been created through gene-splicing techniques of biotechnology or genetic engineering.

The production diagram in FIG. 2 shows the process used to obtain the perilla seed extract in accordance with a non-limiting example. The extraction technology as described relative to the chia seed oil and extract in the incorporated by reference application and described above in some detail may be used. It should be understood that extraction technology creates materials for human nutrition and supplementation and offers various benefits including enhanced efficacy with the isolation of key components to allow higher dosage and targeted performance. Extraction allows standardization. Natural materials tend to vary in make-up and extraction makes them consistent. It is also convenient because smaller dosages of high efficiency materials allow a consumer to more easily obtain the required levels of nutrients in a daily regimen. There is also enhanced safety because extraction gives more of the desired products and less of what is not desired. Extraction allows the removal of compounds that are not optimal for human health from natural materials.

The desired extraction technology uses the DEEP EXTRACT® process from Valensa International as an ultra high pressure carbon dioxide extraction technology that yields micronutrients and has high extraction efficiency to deliver more of the higher molecular weight compounds that more closely track the natural source materials. The process is flexible and allows for possible fractionation of the product if desired and delivery of specific compounds out of the raw material.

This extraction process, such as the DEEP EXTRACT® process, offers a more gentle treatment of high value raw materials at temperature levels that are substantially below those used in other expeller press processes and some chemical solvent extraction processes in the absence of oxygen. This reduces the degradation of liable compounds, chemical change of a component and the oxidation potential. The supercritical CO² process offers virtual sterilization of the finished product and biomass, which are untouched by chemical solvents and stay “natural” as before extraction. Selective fractionation in some example is advantageous. Pressure is a main tool used to tailor the resulting fractionated products for product quality and efficient manufacturing. Because the CO² extraction is an all-natural and organic process, the final product is devoid of impurities and residues and delivers through the supercritical CO² extraction the high molecular weight compounds such as sterols, carotenoids and long chain alcohols.

Supercritical CO² extraction is advantageous over other methods used for extracting botanicals, including tinctures (usually alcohol extraction; steam distillation; expeller pressing, sometimes referred to as “cold pressing,” and chemical solvent extraction). Chemical solvent extraction technology using strong solvents and supercritical CO² technology using high pressures typically offer the most comprehension extraction of a botanical. Supercritical CO² extraction conducted under very high pressure is advantageous. When carbon dioxide gas (CO²) is compressed above 73 bar at a temperature above 31 degrees C. (87.8 degrees Fahrenheit), it transforms into a dense gas as supercritical CO², which has an extremely high solvating capacity and a power to extract constituents of botanicals. Its solvating capacity is a function of its density and by changing its density with pressure, the manufacturer is able to select the quality, quantity and specific principles of the targeted extract. Supercritical CO² is biologically compatible and generally regarded as safe (GRAS) by the FDA. It is also non-flammable and environmentally sound. Any defatted cake resulting from the supercritical CO² process may be viable and can be marketed or used for further processing in a wide range of human/food applications. As will be explained below, the perilla cake that is partially defatted is processed during supercritical extraction to form a flour that can be used as a dietary supplement, food or beverage.

The supercritical CO² process offers a gentle treatment of high value raw materials at temperature levels substantially below those used in expeller press in some chemical solvent extraction operations in the absence of oxygen. This reduces the degradation of labile compounds, chemical changing components and the oxidation potential. The supercritical CO² process offers virtual sterilization of the finished product and biomass that are untouched by chemical solvents and stay “natural” as they were before extraction. It also allows the advantage of fractionating the extracted components selectively with pressure tailoring the resulting fractionated products for product quality and efficient manufacturing. This addresses pesticide/insecticide residues and handle concerns about microorganisms that are present in expeller press materials.

The perilla extract as shown in the flowchart of FIG. 2 is dewatered and decantated and antioxidants added such as the Valensa OTB® per oxidation blocker system as a stabilizer to ensure that the botanical extract reaches a consumer in an efficacious and safe form. Stabilization with the OTB® components is a key to shelf life and continued product quality and is advantageous over using preservatives to stabilize natural materials, which is often seen as a negative by consumers. The OTB® per oxidation blocker system used by Valensa is 100% natural, non-GMO, and protects sensitive oils and particularly the highly unsaturated oils derived from fish and botanicals from the manufacture to consumption. It may also be used to protect the perilla flour as the leftover residue from supercritical CO² extraction. The OTB® per oxidation blacker is a synergistic proprietary formulation of powerful natural compounds including astaxanthin, phenolic antioxidants and natural tocopherols. This technology prevents destructive oxidative, photochemical and rancification reactions. It protects expensive and sensitive compounds such as carotenoids and polyunsaturated fatty acids and can boost the effectiveness of other antioxidants such as vitamin E because it chemically quenches stable vitamin E free radicals. The antioxidants have in-vivo activity to protect both products and people.

Perilla has a number of essential oils. These are extracted from the leaves of perilla. About 50% to about 60% of perillaldehyde is responsible for so much of the aroma and taste of perilla. There are other terpenes such as limonene, caryophyllene and farnesene. There are other chemotypes such as perilla keytone (PK), esholzia keytone (EK), perillene (PL), and various phenylpropanoids such as myristicin, dillapiole and elemicin. Citral is a type rich in rosefuran. Perilla oil typically is obtained by pressing the seeds of perilla that contain about 35% to about 45% oil. In some parts of Asia, perilla oil is an edible oil valued for medicinal benefit. Typically, perilla oil is a rich source of omega-3 fatty acid alpha-linolenic acids. As a drying oil, it is similar to tung oil or linseed oil and is sometimes used in paint, varnish, linoleum, printing ink, lacquers and other protective waterproof coatings. In Japan, the oxime of perillaldehyde (perillartin) is used as an artificial sweetener and typically is about 2,000 times sweeter than sucrose.

Rancimat testing has shown the advantages of the perilla seed oil extract in accordance with a non-limiting example. This method is an accelerated oxidation test that is a simple, quick and efficient way to screen the effectiveness of the antioxidants used in liquid fats and oils. Typically, the rancimat test is an accelerated oxidation test in which the oil or fat to be tested is run at an elevated temperature exposing the sample to air accelerating the oxidation process of the oil. Auto oxidation typically occurs in a few hours instead of the months or years and the metabolites are driven off into a measuring vessel that measures the change in conductivity in one example. This would indicate the point at which the formation of volatile carboxylic acids and oxidation has occurred.

It is also possible to disperse nano- and/or micro-particles of rice or sugar cane based policosanol for providing a heart healthy dietary supplement. Such dietary supplement composition additives are disclosed in commonly assigned U.S. Pat. No. 7,959,950, the disclosure which is hereby incorporated by reference in its entirety. This human or animal dietary supplement composition includes one or more long chain (C24-C36) primary alcohols (policosanols) dispersed in food-grade oils or fats where the average policosanol particle size is greater than 2 microns and less than 10 microns in one example, and in another example, less than 100 microns.

There now follows further details of the composition of matter in accordance with a non-limiting example that is formed as a shelf stable, partially defatted supercritical CO2 fluid solvent extracted whole grain flour derived from the cracked biomass of perilla frutescens. In one example, the flour is formed of minerals and includes about 2 to 8 percent of native seed oil and about 35 to 45 percent protein and about 35 to 45 percent fiber. In one example, the native seed oil is formed of about 1 to about 4 percent ALA and about 0.2 to 0.8 percent LA and in another example, the fiber is about 32 to about 40 percent insoluble fiber and from about 2 to about 6 percent soluble fiber. In another example, the composition exhibits pH dependent thixotropic properties when mixed with water. In another example, the flour is formed of lipophilic additives, such as at least one of rosemary oil, tocopherols, tocotrienols, carotenoids, seed oils, lipophilic solvent extracted botanical oils, lipophilic food flavorings, polyunsaturated fatty acid esters. Hydrophilic additives can include hydrophilic solvent extracts of botanicals, green tea extract, grape seed extract, ascorbic acid, caffeine, mono and/or polysaccharides, gums, phospholipids, biopolymers, or hydrophilic food flavorings.

In another example, about 2 to about 3 percent fructo-oligosaccharides can be used such as forming an antioxidant. The OTB® per oxidation blacker system may be used as described above. A delivery product can be used with the composition that is formed as a beverage, protein shake, nutritional bar, confectionary filling, icing, pasta, processed meat, peanut butter or jelly. This composition may be added to a dietary supplement, food or beverage and used to treat gastrointestinal irregularities or cardiovascular disease in humans or animals. It can be formed as a beverage, liquid concentrate or dried beverage premixed to which the composition is added. In another example, a liquid concentrate or dried premix can be formed that includes protein shakes, fruit smoothies, ready-to-drink beverages, dried beverage pre-mixes, frozen fruit concentrates, acqueous alcoholic beverage premixes, concentrates or their dried pre-mixes, vitamin, carbohydrate and protein fortified meal replacement beverages, drinkable dairy and non-dairy yogurts, gravies and dried gravy pre-mixes and ready-to-drink and dried pre-mixed infant formulas. The final beverage may be thickened by adding one or more acidulants for adjusting the pH from between about 3 to about 6.5.

FIG. 3 shows a production diagram as a flowchart for producing the described composition of matter as a shelf stable, partially defatted supercritical CO2 fluid solvent extracted whole grain flour that is derived from the cracked biomass of perilla frutenscens. As illustrated, the process starts (block 158) and the perilla frutenscens seed is obtained (block 160) for further processing. The seed is cracked (block 162) and subject to extraction (block 164) using the supercritical CO2 fluid solvent extraction followed by CO2 separation (block 166) and carbon dioxide recycling (block 168). The seed oil is obtained (block 170). The defatted grain is collected (block 172) and packaged (block 174) and then subject to quality control analysis (block 176). The process ends (block 178).

The product specification for the composition in one non-limiting example follows:

Ingredient: Perilla ( Perilla frutescens) seed (partially defatted with supercritical CO₂) Kosher certified by KSA; IFANCA Halal Physical Appearance Brown-beige coarse powder Taste Mild Bulk Density 0.15-0.25 g/mL Chemical Fat 2-8% Hexane Soxhlet Omega-3 (ALA) 1-4 g/100 g (as-is) GC-FAME Protein 35-45% Fiber 35-45% Pesticides No detectable pesticide residues CDFA or similar (>RL) on seed raw material used to manufacture product Microbiological USP <61> Total Plate Count max. 10⁴/g Yeast/Mold max. 10³/g E. coli/Coliforms <10/g

Although hexane soxhlet is disclosed, it should be understood that different extraction may be used. It should be understood that a range of values is given. These values may vary even more by as much as twenty percent.

There now follows a representative analysis of the composition as an omega-3 low fat whole grain flour.

Ingredient: Perilla ( Perilla frutescens) Seed (partially defatted with supercritical CO₂) Dietary Calories 220 kcal/100 g Fat   4 g/100 g Saturated Fat 0.3 g/100 g Monounsaturated Fat 0.8 g/100 g Omega-3 ALA   2 g/100 g Omega-6 LA 0.4 g/100 g Total dietary fiber RDI (25 g)  40 g/100 g Insoluble fiber  36 g/100 g Soluble fiber   4 g/100 g Minerals: US RDI (mg) mg/100 g Sodium 2400 3 Potassium 3500 1100 Calcium 1000 680 Iron 18 <1 Phosphorus 1000 3 Magnesium 400 500 Arsenic — <0.5 Mercury — <0.5 Cadmium — <0.5 Lead — <0.5 Ash 6.4% Amino acids: g/100 g alanine 1.7 arginine 4.4 aspartic acid 3.1 cysteine 0.6 glutamic acid 6.8 glycine 1.8 histidine 1.0 isoleucine 1.4 leucine 2.4 lysine 1.4 methionine 0.7 phenylalanine 1.9 proline 1.3 serine 1.9 threonine 1.3 tryptophan 0.6 tyrosine 1.4 valine 1.8 Protein (Kjeldahl)  42 g/100 g

The ingredient listing with dietary calories, fat, total dietary fiber, minerals, including ash and amino acids, have specific numbers as a non-limiting example, but these numbers can vary by as much as 10 to about 25 percent depending upon the final product and processing parameters used during the supercritical fluid extraction processing. The parameters of the superfluid processing can be varied to form the final product depending on what final product composition is desired. Pressure is one particular parameter that can be varied to form a selected final product. Also, the nature of the milling or roller press flaking of the perilla frutenscens seed to obtain a cracked seed biomass can be varied to form the final product. The amount of cracking can be relevant to the amount of extraction during the supercritical fluid extraction process. Also, fractionation may be used during the CO² extraction as described above. The CO² extraction such as used by the assignee Valensa has a high solvating capacity that is a function of density. By changing the density (with pressure), the CO² extractor is able to select the quality, quantity and specific principles of the targeted extract and flour. The output from the supercritical CO² extractor depends on the change in density, pressure and other extractor parameters. For example, it is possible to fractionate during the supercritical CO² extraction in separate pressure step-down stages and light and heavy fractions of seed oil extract collected, but with the flour being separate.

In accordance with non-limiting aspects, it has been found that the partially defatted perilla derived whole grain flour is stable. This resulting flour's stability serves as a stable delivery platform for the essential fatty acid esters of ALA, LA, protein, soluble and insoluble fiber, minerals such as calcium, potassium, magnesium and phosphorus, and both lipophilic and hydrophilic additives, which is free of cyanogenic glycosides, vitamin B antagonists, lignin and gluten. The resulting flour can be used as a food ingredient in a beverage and as a dietary supplement ingredient to various foods. This perilla derived flour can provide beneficial results in enhancing gastrointestinal regularity and heart health.

The resulting partially defatted whole grain perilla derived flour may exhibit an ability to reabsorb large quantities of lipophilic as well as hydrophilic additives while exhibiting a pH dependent thixotropic effect in aqueous environments. The flour may be formed as a food or beverage or dietary supplement ingredient and operate as a delivery vehicle for lipophilic and hydrophilic additives in the presence of protein, fiber, various levels of the essential fatty acid esters of ALA and LA and minerals that are free of cyanogenic glycosides, vitamin B antagonists, lignin and gluten.

In accordance with a non-limiting aspect, the resulting perilla derived flour may enhance the protein, fiber, mineral content and pH controlled viscosity of beverages and their liquid concentrates, dried beverage pre-mixes including protein shakes and fruit smoothies, ready-to-drink beverages, beverage pre-mixes, frozen fruit concentrates, alcoholic beverage dry pre-mixes and concentrates, meal replacement beverages, drinkable dairy and non-dairy yogurts, gravies and dry gravy pre-mixes, and ready to drink and dried pre-mixed infant formulas.

The resulting seed meal as a flour provides a unique blend of protein, insoluble and soluble fiber, and variable amounts of the essential fatty acid triglycerides of alpha-linolenic acid (omega-3, “ALA”) and linoleic acid (omega-6, “LA”).

The resulting flour can be incorporated into beverages, dry beverage pre-mixes, liquid or frozen beverage concentrates and the like with the added feature of pH controlled viscosity by either the amount of perilla derived meal or flour that is added and/or by optionally lowering the pH with an acidulant to improve further the viscosity of the resulting beverage.

In one aspect, the perilla derived flour is added to a beverage, liquid concentrate, or dried beverage pre-mixes. The flour may be used for prepared beverages, their liquid concentrates, and dried pre-mixes, including protein shakes, fruit smoothies, ready to drink beverages, dry beverage pre-mixes, frozen fruit concentrates, aqueous alcoholic beverage pre-mixes, concentrates or their dried pre-mixes, vitamin, carbohydrate and protein fortified meal replacement beverages, drinkable dairy and non-dairy yogurts, gravies and dry gravy pre-mixes, and ready to drink and dried pre-mixed infant formulas. The flour may include added lipophilic additives and added hydrophilic additives. The pH range may be adjusted with the addition of one or more acidulants to bring the pH of the final product to a pH of from about 3 to about 6.5 in an example to further thicken the resulting beverage in one non-limiting example.

The flour may be added to a beverage and prepared in a pasteurized beverage form. In its use, it is shelf stable and contains sterilized whole seed in an admixture with a wide range of liquid beverage components, including but not limited to, for example, fruit derived juices, water or natural or artificially flavored water such as colas, coffees, teas and the like. It can contain a sweetener such as sucrose, fructose corn syrup or an artificial sweetener. It can also contain preservatives such as sodium benzoate and such other additives common to beverage formulations. The resulting beverage may exhibit a pH dependent viscosity. The resulting beverage may be rich in fiber and is particularly useful for maintaining good gastrointestinal system regularity in a convenient and tasty beverage form while delivering heart healthy polyunsaturated fatty acids, protein and minerals.

The beverage can be enriched in protein, polyunsaturated essential fatty acid triglycerides, minerals and rich in fiber particularly useful for maintaining good gastro-intestinal system regularity in a convenient and tasty beverage form while delivering heart healthy polyunsaturated fatty acids, protein and minerals requiring no additional thickening agents. It can be useful for the control of hunger via satiety requiring no additional thickening agents to effect such satiety.

The resulting flour can be incorporated into beverages, dietary supplement bars, nutritional bars, baked goods, confectionary fillings, icings, processed meats, peanut butter, jellies and the like as delivery vehicle for quantities of the essential fatty acid esters of ALA and LA, protein, soluble and insoluble fiber, and minerals depending on the amount of ALA and LA retained in the partially defatted flour and the amount of the flour employed in the end user formulation.

In addition, the resulting partially defatted whole grain flour is capable of re-absorbing and stabilizing relatively large quantities of other lipophilic compounds providing a convenient vehicle for delivery of these compounds in addition to ALA, LA, protein, insoluble fiber and minerals as an ingredient in food, beverage and dietary supplement based formulations. In one example, the partially defatted whole grain flour can reabsorb lipophilic compounds of from about 1 to about 25 percent of the weight of the partially defatted whole grain flour, depending on the level of native seed oil remaining in the solvent extracted, whole grain flour.

In an example, the resulting flour also exhibits unique pH dependent thixotropic properties when added to aqueous based formulations such as beverages, including protein-based smoothies. It also provides a unique method or process for mitigating the undesirable free water associated with nutritional and dietary bar production, while providing ALA, LA, protein, soluble and insoluble fiber and minerals to such formulations and providing other lipophilic compounds depending on the composition of the flour employed.

In one aspect, the flour is used with a beverage or protein shake “smoothie” or nutritional bar or dietary supplement bar enriched in protein, fiber, minerals and a controlled portion of ALA and LA. The flour also can be used with a confectionary filling enriched in protein, fiber, minerals and a controlled portion of ALA and LA. It can also be used with an icing or processed meat or peanut butter or jelly enriched in protein, fiber, minerals and a controlled portion of ALA and LA.

The flour can also be used with a chocolate, pectin or gelatin based confectionary or dietary supplement whose inner filling, outer shell or integrated composition is enriched in protein, fiber, minerals and a controlled portion of ALA and LA. It can be used with a pasta enriched in protein, fiber, minerals and a controlled portion of ALA and LA.

As noted before, using the super-critical CO₂ fluid extraction method of preparation, the resulting flour can be incorporated into beverages, dietary supplement bars, nutritional bars, baked goods, confectionary fillings, icings, processed meats, peanut butter, jellies and the like as a partially soluble delivery vehicle for heart healthy quantities of the essential fatty acids ALA and LA, protein and soluble and insoluble fiber depending on the amount employed in the end user formulation.

In another aspect, the flour can include lipophilic compounds reabsorbed into the flour including one of at least rosemary oil, tocopherols, tocotrienols, carotenoids, seed oils, lipophilic solvent extracted botanical oils, lipophilic food flavorings or other health or functional hydrophilic compounds.

In another aspect, the flour can include hydrophilic additives re-absorbed into the flour such as, for example, hydrophilic solvent extracts of botanicals, green tea extract, grape seed extract, ascorbic acid, caffeine, mono and/or polysaccharides, gums, phospholipids, biopolymers, hydrophilic food flavorings or other health or functional hydrophilic compounds. In yet another aspect, the flour may include a suitable proteolytic enzyme or plurality of enzymes to produce a novel probiotic mixture rich in essential amino acids. It can also be treated with a suitable cellulase or amylase enzyme or enzymes, which degrades the soluble and insoluble fiber to produce a novel probiotic mixture rich in digestible monosaccharide and oligosaccharide units in another example.

The resulting perilla derived flour can also be incorporated into beverages, dietary supplement bars, nutritional bars, baked goods, confectionary fillings, icings, processed meats, peanut butter, jellies, bakery goods and the like as a delivery vehicle for protein, soluble and insoluble fiber and minerals or as a desiccant in food applications where excess water creates a formulation problem.

Many modifications and other embodiments of the invention will come to the mind of one skilled in the art having the benefit of the teachings presented in the foregoing descriptions and the associated drawings. Therefore, it is to be understood that the invention is not to be limited to the specific embodiments disclosed, and that the modifications and embodiments are intended to be included within the scope of the dependent claims. 

That which is claimed is:
 1. A composition of matter comprising a shelf stable, partially defatted supercritical CO2 fluid solvent extracted whole grain flour derived from a cracked biomass of perilla frutescens, the flour comprising minerals and 2 to 8 percent of native seed oil, 35 to 45 percent protein, and 35 to 45 percent fiber.
 2. The composition according to claim 1, wherein the native seed oil comprises 1 to 4 percent ALA and 0.2 to 0.8 percent LA.
 3. The composition according to claim 1, wherein the fiber comprises 32 to 40 percent insoluble fiber and 2 to 6 percent soluble fiber.
 4. The composition according to claim 1, wherein the composition exhibits pH dependent thixotropic properties when mixed with water.
 5. The composition according to claim 1, wherein the flour further comprises lipophilic additives comprising at least one of rosemary oil, tocopherols, tocotrienols, carotenoids, seed oils, lipophilic solvent extracted botanical oils, lipophilic food flavorings, polyunsaturated fatty acid esters.
 6. The composition according to claim 1, wherein the flour further comprises hydrophilic additives comprising at least one of hydrophilic solvent extracts of botanicals, green tea extract, grape seed extract, ascorbic acid, caffeine, mono and/or polysaccharides, gums, phospholipids, biopolymers, or hydrophilic food flavorings.
 7. The composition according to claim 1, further comprising 2 to 3 percent of fructo-oligosaccharides.
 8. The composition according to claim 1, and further comprising a delivery product comprising a beverage, protein shake, nutritional bar, confectionary filling, icing, pasta, processed meat, peanut butter or jelly.
 9. A composition of matter comprising a shelf stable, partially defatted, perilla frutescens derived, whole grain flour comprising minerals and 2 to 8 percent of native seed oil, 35 to 45 percent protein, and 35 to 45 percent fiber, wherein the perilla frutescens derived, whole grain flour is made by pre-milling or roller press flaking perilla frutescens seed in the absence of oxygen to obtain a cracked seed biomass and subjecting the cracked seed biomass to supercritical fluid CO2 extraction to produce the flour with or without lipophilic and/or hydrophilic antioxidants.
 10. The composition according to claim 9, wherein the native seed oil comprises 1 to 4 percent ALA and 0.2 to 0.8 percent LA.
 11. The composition according to claim 9, wherein the fiber comprises 32 to 40 percent insoluble fiber and 2 to 6 percent soluble fiber.
 12. The composition according to claim 9, wherein the composition exhibits pH dependent thixotropic properties when mixed with water.
 13. The composition according to claim 9, comprising lipophilic additives within the flour comprising at least one of rosemary oil, tocopherols, tocotrienols, carotenoids, seed oils, lipophilic solvent extracted botanical oils, lipophilic food flavorings, polyunsaturated fatty acid esters.
 14. The composition according to claim 9, comprising hydrophilic additives within the flour comprising at least one of hydrophilic solvent extracts of botanicals, green tea extract, grape seed extract, ascorbic acid, caffeine, mono and/or polysaccharides, gums, phospholipids, biopolymers, or hydrophilic food flavorings.
 15. The composition according to claim 9, comprising 2 to 3 percent of fructo-oligosaccharides.
 16. The composition according to claim 9, comprising a delivery product comprising a beverage, protein shake, nutritional bar, confectionary filling, icing, pasta, processed meat, peanut butter or jelly.
 17. A method of treating gastrointestinal irregularities or cardiovascular disease in humans or animals by administering an effective amount of a dietary supplement, food or beverage that has added thereto a composition comprising a shelf stable, partially defatted supercritical CO2 fluid solvent extracted whole grain flour derived from a cracked biomass of perilla frutescens, the flour comprising minerals and 2 to B percent of native seed oil, 35 to 45 percent protein, and 35 to 45 percent fiber.
 18. The method according to claim 17, and further comprising forming a beverage, liquid concentrate, or dried beverage pre-mixes to which the composition is added.
 19. The method according to claim 17, and further comprising preparing liquid concentrates or dried pre-mixes including protein shakes, fruit smoothies, ready-to-drink beverages, dry beverage pre-mixes, frozen fruit concentrates, aqueous alcoholic beverage pre-mixes, concentrates or their dried pre-mixes, vitamin, carbohydrate and protein fortified meal replacement beverages, drinkable dairy and non-dairy yogurts, gravies and dry gravy pre-mixes, and ready-to-drink and dried pre-mixed infant formulas.
 20. The method according to claim 19, and further comprising thickening the resulting final beverage by adding one or more acidulants for adjusting the pH from between about 3 to about 6.5. 